Antimicrobial compounds and methods of making and using the same

The present refers to the field of antimicrobial compounds and to the methods for preparing and using them. These compounds are useful for treating, preventing, and reducing the risk of microbial infections in humans and animals. Claim 1: A compound characterized in that it has the formula (1), (2), (3) or (4) where -GHJ is selected, alternatively, from -G (HJ) (HJ), where each H and J is selected independently of, CBA-, -DEF, and -GHJ are chemical portions, where A, D, and G are independently selected from the group consisting of: (a) a single bond, (b) C1-8alkyl, (c) C2-8alkenyl, (d) C2-8alkynyl, where i) 0-4 carbon atoms in any of (b) - (d) immediately above, it is optionally replaced by a portion selected from the group consisting of -O-, S (O) p, -NR6-, - (C = O) -, -S (O) pNR6-, -NR6S (O) p -, and -NR6S (O) pNR6-, ii) any of (b) - (d) immediately above, is optionally substituted with one or more R5 groups, and iii) any of (b) - (d) immediately above, it is optionally substituted with C 1-8 -R5 alkyl groups; (e) -O-, (f) -NR6-, (g) -S (O) p-, (h) -C (O) -, (i) -C (O) O-, (j) - OC (O) -, k) -OC (O) O-, (l) -C (O) NR6-, (m) -NR6CO-, (n) -NR6C (O) NR6-, (o) -C (= NR6) -, (p) -C (= NR6) O-, (q) -OC (= NR6) -, (r) -C (= NR6) NR6-, (s) -NR6C (= NR6) -, (t) -C (= S) -, (u) -C (= S) NR6-, (v) -NR6C (= S) -, (w) -C (O) S-, (x) -SC (O) -, (y) -OC (= S) -, (z) -C (= S) O-, (aa) -NR6 (CNR6) NR6-, (bb) -CR6R6C (O) - , (cc) -C (O) NR6 (CR6R6) t-, (dd) a saturated heterocycle, 3-14 membered unsaturated or aromatic containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, or (ee) a 3-14 saturated, unsaturated or aromatic carbocycle, and (ff) - (CR6R6) t -, where (dd) or (ee) is optionally substituted with one or more R5 groups; B, E, and H are independently selected from the group consisting of: (a) a single bond, (b) a 3-14 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, (c) a saturated, unsaturated, or aromatic carbocycle of 3-14 members, where (b) or (c) is optionally substituted with one or more groups (d) C1-8alkyl, (e) C2-8alkenyl, (f) C2-8alkynyl, where i) 0- 4 carbon atoms in any of (d) - (f) immediately above, is optionally replaced by a portion selected from the group consisting of -O-, -S (O) p-, -NR6-, - (C = O) -, -C (= NR6) -, -S (O) pNR6- , -NR6S (O) p-, and -NR6S (O) pNR6-, ii) any of (d) - (f) immediately above is optionally substituted with one or more R5 groups, and iii) any of (d) - (f) immediately above is optionally substituted with C1-8-R5 alkyl groups; and (g) - (CR6R6) t-, C, F, and J are independently selected from the group consisting of: (a) hydrogen, (c) F, (d) CI, (e) Br, (f) I, (g) -CF3, (h) -CN, (i) -N3; (j) -NO2, (k) -NR6 (CR6R6) tR8, (l) -OR8, (m) -S (O) p (CR6R6) tR8, (n) -C (O) (CR6R6) tR8, ( o) -OC (O) (CR6R6) tR8, (p) -SC (O) (CR6R6) tR8, (q) -C (O) O (CR6R6) tR8, (r) -NR6C (O) (CR6R6) tR8, (s) -C (O) NR6 (CR6R6) tR8, (t) -C (= NR6) (CR6R6) tR8, (u) -C (= NNR6R6) (CR6R6) tR8, (v) -C ( = NNR6C (O) R6) (CR6R6) tR8, (w) -C (= NOR8) (CR6R6) tR8, (x) -NR6C (O) O (CR6R6) tR8, (y) -OC (O) NR6 ( CR6R6) tR8, (z) -NR6C (O) NR6 (CR6R6) tR8, (aa) -NR6S (O) p (CR6R6) tR8, (bb) -S (O) pNR6 (CR6R6) tR8, (cc) - NR6S (O) pNR6 (CR6R6) tR8, (dd) -NR6R8, (ee) -NR6 (CR6R6) R8, (ff) -OH, (gg) -NR8R8, (hh) -OCH3, (ii) -S (O) pR8, (jj) -NC (O) R8, (kk) -NR6C (NR6) NR6R8, (ll ) a C1-8 alkyl group, (mm) C2-8 alkenyl group, (nn) C2-8 alkynyl group, (oo) a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of in nitrogen, oxygen and sulfur, (pp) a 3-14 membered saturated, unsaturated or aromatic carbocycle, (qq) - (CR6R6) tNR6 (CR6R6) tR8, (rr) -N [(CR6R6) tR8] [C = O (CR6R6) tR8], (ss) - (CR6R6) tN [(CR6R6) tR8] [(CR6R6) tR8], (tt) - (CR6R6) tNR6 (C = O) (CR6R6) tR8, (uu) -haloalkyl, (vv) -C (O) (CR6) [(CR6R6) tR8] R8, (ww) - (CR6R6) tC (O) NR8R8, (xx) - (CR6R6) tC (O) O (CR6R6) tR8, (yy) -NR6C ( O) CR8R8R8, (zz) -N [(CR6R6) tR8] C (O) R8, and (aaa) -S (O) pNR8R8; where (ll) to (pp) are optionally substituted with one or more R7 groups; R5 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3 (i) - NO2, (j) -NR6R6, (k) -OR8, (l) -NR6 (CNR6) NR6R6, (m) C1-8 alkyl, (n) C1-8 alkenyl, (o) C1-8 alkynyl, (p ) -C1-8alkyl- (a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur), (q) -C1-8alkyl- (carbocycle 3-14 membered saturated, unsaturated or aromatic), (r) -haloalkyl, (s) -SR6, (t) 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and (u) saturated, unsaturated or aromatic carbocycle of 3 -14 members; alternatively, two R5 groups are taken together to form a carbocycle where (m) to (r) and (t) to (u) are optionally substituted with one or more R8; R6 is selected from (a) hydrogen, (b) C1-8alkyl or alternatively two R6 groups are taken together to form a carbocycle, (c) -haloalkyl, (d) a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and (e) 3-14 membered saturated, unsaturated, or aromatic carbocycle; where (b) to (e) are optionally substituted with one or more R8; R7 is selected from (a) hydrogen, (b) F, (c) CI, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) - NO2, (j) -NR6R6, (k) -OR6, (l) -NR6 (CNR6) NR6R6, (m) C1-8 alkyl, (n) C1-8 alkenyl, (o) C1-8 alkynyl, ( p) -C1-8alkyl- (saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) C1-8alkyl- (saturated carbocycle , unsaturated or 3-14 membered aromatic), (r) haloalkyl-, (s) -NR6R8, (t) -OR8, (u) - (CR6R6) tNR6R8, (v) -CR6R8R8, (w) -SR6, (x) 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (y) 3-14 membered saturated, unsaturated or aromatic carbocycle, (z) - (CR6R6) tC (O) NR8R8, (aa) -S (O ) pR8, (bb) -NR6C (O) NR6R6, (cc) -NR6C (O) R6, (dd) -C (= NR6) NR6R6; where (m) to (q) and (x) to (y) are optionally substituted with one or more R9; R8 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R9, (k) -OR9, (l) -NR6 (CNR6) NR6R6, (m) C1-8 alkyl, (n) C1-8 alkenyl, (o) C1-8 alkynyl, ( p) -C1-8alkyl- (saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) C1-8alkyl- (saturated carbocycle , unsaturated or 3-14 membered aromatic), (r) saturated heterocycle, 3-14 membered unsaturated or aromatic containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (s) 3-14 membered saturated, unsaturated or aromatic carbocycle, (t) -haloalkyl, (u) -C (O) (CR6R6) tR9, (v) -SR6, (w) -OC (O) (CR6R6) tR9, (x) -NR6C (O) NR6R9, (y) -NR6C (O) R9, ( z) -NR6 (CNR9) (NR6R6), (aa) -ONR6 (CNR6) NR6R6, (bb) -C (= NR9) NR6R6, (cc) -S (O) pR9, (dd) - (CR6R6) tC (O) NR6R9, (ee) - (CR6R6) tOR9, and (ff) - (CR6R6) tNR6R9; where (m) to (s) are optionally substituted with one or more R9; R9 is selected from (a) hydrogen, (b) F, (c) CI, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R10, (k) -OR6, (l) -NR6 (CNR6) NR6R6, (m) -C (O) (CR6R6) tNR6R6, (n) C1-8-alkyl, (o) alkenyl C1-8, (p) C1-8 alkynyl, (q) 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (r) saturated carbocycle, 3-14 membered unsaturated or aromatic, (s) -haloalkyl, (t) - (CR6R6) tOR6, (u) -O (CR6R6) tNR6R10, (v) -C (O) R6, (w) -SR6, (x) -C (O) OR10, (y) -S (O) pR6, (z) -C 1-8 alkyl- (3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (aa) C1-alkyl -8- (3-14 membered saturated, unsaturated or aromatic carbocycle), (bb) -O (CR6R6) tOR6, (cc) -C (= NR6) NR6R6, (dd) -ONR6R6, (ee) -NR6C ( O) NR6R6, (ff) -O (CR6R6) tOR6, (gg) -NR6C (O) R6, and (hh) - (CR6R6) tNR6R10; where (n) to (r) and (z) to (aa) are optionally substituted with one or more R10; R10 is selected from (a) hydrogen, (b) F, (c) CI, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R6, (k) -OR6, (l) -NR6 (CNR6) NR6R6, (m) -C (O) (CR6R6) tNR6R6, (n) C1-8 alkyl, (o) alkenyl C1-8, (p) C1-8 alkynyl, (q) 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (r) saturated carbocycle, 3-14 membered unsaturated or aromatic, (s) -haloalkyl, (t) - (CR6R6) tOR6, (u) -O (CR6R6) tNR6R6, (v) -C (O) R6, (w) -SR6, (x) -C (O) OR6, (y) -S (O) pR6, (z) -C 1-8 alkyl- (3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (aa) C1-alkyl -8- (3-14 membered saturated, unsaturated or aromatic carbocycle), (bb) -O (CR6R6) tOR6, (cc) -C (= NR6) NR6R6, (dd) -ONR6R6, (ee) -NR6C ( O) NR6R6, (ff) -O (CR6R6) tOR6, (gg) -NR6C (O) R6, and (hh) - (CR6R6) tNR6R6; optionally, where either the -DEF group or the -GHJ group is absent, but both -DEF and -GHJ are not simultaneously absent; p is 0, 1s 2, and t is 0, 1, 2, or 3, or a salt, ester, tautomer, or prodrug thereof.